Jump to main content
Jump to site search

Issue 22, 2017
Previous Article Next Article

Molecular packing and the handedness of the self-assemblies of C17H35CO-Ala-Phe sodium salts

Author affiliations

Abstract

The handedness of the self-assemblies of several series of homogeneous lipodipeptide sodium salts is controlled by the chirality of the amino acid at the C-terminus. This phenomenon is named the “C-terminal determination” rule. Herein, four heterogeneous C17H35CO-Ala-Phe sodium salts, designed and synthesized by changing the chirality of the amino acids, were able to self-assemble into twisted nanoribbons in deionized water. The handedness of the nanoribbons was controlled by the chirality of the alanine, which does not follow the “C-terminal determination” rule. This phenomenon might be because the homochiral and heterochiral lipodipeptide sodium salt molecules packed into different structures. The X-ray diffraction and circular dichroism characterizations indicated that the molecules self-assembled into an interdigitated bilayer structure and there were no strong π–π stackings between neighboring phenyl groups.

Graphical abstract: Molecular packing and the handedness of the self-assemblies of C17H35CO-Ala-Phe sodium salts

Back to tab navigation

Supplementary files

Publication details

The article was received on 14 Jul 2017, accepted on 25 Sep 2017 and first published on 26 Sep 2017


Article type: Paper
DOI: 10.1039/C7NJ02553J
Citation: New J. Chem., 2017,41, 13253-13259
  •   Request permissions

    Molecular packing and the handedness of the self-assemblies of C17H35CO-Ala-Phe sodium salts

    S. Lin, Y. Li, B. Li and Y. Yang, New J. Chem., 2017, 41, 13253
    DOI: 10.1039/C7NJ02553J

Search articles by author

Spotlight

Advertisements